$69+ Cheap flights from Midway (MDW) to Pittsburgh (PIT)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PIT
Sep 3 — Sep 101
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Pittsburgh with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Pittsburgh
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Best
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Cheapest flights from Midway to PittsburghExplore the most affordable flight options available from Midway to Pittsburgh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
Explore the most affordable flight options available from Midway to Pittsburgh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:10 pm -
Nonstop1h 25m
Sun 9/66:20 pm -
1 stop3h 35m
Deal found 8/3![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:35 pm -
1 stop4h 15m
Tue 9/87:20 pm -
1 stop3h 35m
Deal found 7/30![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:39 pm -
1 stop5h 55m
Sun 9/66:29 pm -
1 stop5h 07m
Deal found 8/3![Delta logo]()
$158
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:10 pm -
Nonstop1h 25m
Mon 9/77:30 pm -
Nonstop1h 20m
Deal found 7/31![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:50 am -
2 stops10h 00m
Fri 9/115:35 am -
2 stops10h 55m
Deal found 8/3![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:45 am -
Nonstop1h 25m
Tue 9/83:25 pm -
1 stop4h 20m
Deal found 7/31![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:20 am -
2 stops8h 00m
Sat 9/51:55 pm -
1 stop6h 25m
Deal found 8/1![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:20 pm -
Nonstop1h 30m
Tue 9/226:55 pm -
Nonstop1h 25m
Deal found 8/1![Southwest logo]()
$191
Best flights from Midway to PittsburghDiscover carefully curated flight deals from Midway to Pittsburgh that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
Discover carefully curated flight deals from Midway to Pittsburgh that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:20 am -
2 stops8h 05m
Sun 9/62:10 pm -
Nonstop1h 30m
Deal found 8/3![Southwest logo]()
$152
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:48 am -
1 stop4h 27m
Thu 9/176:00 am -
1 stop4h 07m
Deal found 7/30![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:30 am -
1 stop4h 35m
Wed 9/163:25 pm -
2 stops8h 00m
Deal found 7/30![Southwest logo]()
$162
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:19 pm -
1 stop4h 39m
Sat 9/1911:35 am -
1 stop7h 24m
Deal found 8/3![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:30 am -
1 stop4h 35m
Tue 9/86:55 pm -
Nonstop1h 25m
Deal found 8/4![Southwest logo]()
$201
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:40 am -
1 stop7h 30m
Tue 9/222:00 pm -
Nonstop1h 25m
Deal found 8/1![Southwest logo]()
$201
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:45 am -
Nonstop1h 35m
Wed 9/2310:10 am -
2 stops7h 40m
Deal found 8/2![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:35 pm -
2 stops6h 15m
Thu 9/32:45 pm -
Nonstop1h 20m
Deal found 7/30![Southwest logo]()
$225
Last-minute flights from Midway to PittsburghDiscover last-minute flight deals from Midway to Pittsburgh. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Pittsburgh. Data last updated August 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:20 am -
2 stops8h 00m
Sat 9/51:55 pm -
1 stop6h 25m
Deal found 8/1![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:05 am -
1 stop4h 50m
Sun 9/62:10 pm -
Nonstop1h 30m
Deal found 7/31![Southwest logo]()
$147
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:39 pm -
1 stop5h 55m
Sun 9/66:29 pm -
1 stop5h 07m
Deal found 8/3![Delta logo]()
$158
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:10 pm -
Nonstop1h 25m
Mon 9/77:30 pm -
Nonstop1h 20m
Deal found 7/31![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:50 am -
2 stops10h 00m
Fri 9/115:35 am -
2 stops10h 55m
Deal found 8/3![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:45 am -
Nonstop1h 25m
Tue 9/83:25 pm -
1 stop4h 20m
Deal found 7/31![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:50 am -
1 stop6h 40m
Sun 9/67:40 pm -
1 stop4h 05m
Deal found 8/4![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:20 pm -
Nonstop1h 30m
Tue 9/222:00 pm -
Nonstop1h 25m
Deal found 8/1![Southwest logo]()
$191
One-way flights from Midway to PittsburghSearch for one-way flight options from Midway to Pittsburgh. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
Search for one-way flight options from Midway to Pittsburgh. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:40 pm -
Nonstop1h 30m
Deal found 8/4![Southwest logo]()
$69
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:31 pm -
1 stop4h 53m
Deal found 8/3![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:15 am -
Nonstop1h 30m
Deal found 7/31![Southwest logo]()
$96
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:10 am -
1 stop6h 30m
Deal found 8/3![Southwest logo]()
$106
This KAYAK deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:05 pm -
Nonstop1h 25m
Deal found 8/4![Southwest logo]()
$131
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:05 am -
1 stop5h 47m
Deal found 8/3![Delta logo]()
$140
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:40 pm -
Nonstop1h 25m
Deal found 7/30![Southwest logo]()
$142
Find flight deals from Midway to Pittsburgh
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Pittsburgh (PIT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $147 (Southwest) |
One-way from | $69 (Southwest) |
Popular in | February |
Cheapest in | September |
Average price | $229 |
Good round-trip deal | $283 or less |
Good one-way deal | $214 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Pittsburgh that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 4, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Pittsburgh that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Sat 9/5
9:20 am-6:25 pm
2 stops8h 05m
Pittsburgh
Sun 9/6
2:10 pm-2:40 pm
Nonstop1h 30m
$152
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Tue 9/15
10:48 am-4:15 pm
1 stop4h 27m
Pittsburgh
Thu 9/17
6:00 am-9:07 am
1 stop4h 07m
$157
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Wed 9/9
6:30 am-12:05 pm
1 stop4h 35m
Pittsburgh
Wed 9/16
3:25 pm-10:25 pm
2 stops8h 00m
$162
Quickest round-trip
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Tue 9/1
6:30 am-12:05 pm
1 stop4h 35m
Pittsburgh
Tue 9/8
6:55 pm-7:20 pm
Nonstop1h 25m
$201
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Tue 9/15
9:40 am-6:10 pm
1 stop7h 30m
Pittsburgh
Tue 9/22
2:00 pm-2:25 pm
Nonstop1h 25m
$201
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Wed 9/16
8:45 am-11:20 am
Nonstop1h 35m
Pittsburgh
Wed 9/23
10:10 am-4:50 pm
2 stops7h 40m
$206
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Thu 9/17
1:19 pm-6:58 pm
1 stop4h 39m
Pittsburgh
Sat 9/19
11:35 am-5:59 pm
1 stop7h 24m
$211
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Thu 8/27
2:35 pm-9:50 pm
2 stops6h 15m
Pittsburgh
Thu 9/3
2:45 pm-3:05 pm
Nonstop1h 20m
$225
Cheapest one-way
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Mon 11/2
4:19 pm-12:46 am
1 stop7h 27m
$79
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Mon 8/31
4:39 pm-12:36 am
1 stop6h 57m
$79
Showing 1-10 of 19 resultsSorted by cheapest first
Compare providers for flights from Midway to Pittsburgh
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Pittsburgh in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Pittsburgh flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Pittsburgh flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Pittsburgh flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Pittsburgh flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Pittsburgh flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Pittsburgh
Have a flexible travel schedule? Discover the best time to fly to Pittsburgh from Midway with our price prediction graph.
MDW-PIT
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Pittsburgh
Prices
Delays
How often are flights from Chicago to Pittsburgh delayed?
About 16% of weekly flights between Chicago and Pittsburgh have experienced delays in the past year, with the average delay time being 103 minutes.
What is the most punctual flight time for Chicago to Pittsburgh flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Pittsburgh flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 15% of flights being delayed.
The best insider tips for Chicago Midway Airport to Pittsburgh flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Pittsburgh trip
Our travel experts
Reviews of airlines servicing Pittsburgh
Get insights into the airlines that provide service to Pittsburgh. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Pittsburgh. Reviews last updated August 4, 2026.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to Pittsburgh. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to Pittsburgh. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Pittsburgh?
Book flights to Pittsburgh if you plan to visit one of these locationsMonroeville
Washington
Chester
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Wexford
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Midway and Pittsburgh flights
Browse other Midway and Pittsburgh flight options. Last updated on August 4, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on August 4, 2026.
Other flights to Pittsburgh
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Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to Pittsburgh
Discover the top airline that operate flights from Midway to Pittsburgh. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$134 | Average$311 | FlexibilityNo cancel fee | On-time63% |